NP-MRD: Showing NP-Card for methyl (1r,4s,4as,7r,8s,9r,10ar)-4,8,9-tris(acetyloxy)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate (NP0329896)

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Record Information

Version

2.0

Created at

2022-09-12 14:44:38 UTC

Updated at

2022-09-12 14:44:38 UTC

NP-MRD ID

NP0329896

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,4s,4as,7r,8s,9r,10ar)-4,8,9-tris(acetyloxy)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate

Description

ZINC8382397 belongs to the class of organic compounds known as 16-oxosteroids. These are steroid derivatives carrying a C=O group at the 16-position of the steroid skeleton. methyl (1r,4s,4as,7r,8s,9r,10ar)-4,8,9-tris(acetyloxy)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate is found in Lycopus europaeus. Based on a literature review very few articles have been published on ZINC8382397.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122216442D          

 35 37  0  0  1  0            999 V2000
    5.4217    0.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6465    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 73 75  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309122216442D          

 35 37  0  0  1  0            999 V2000
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 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 20 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  1  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329896

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]1(C)CC[C@H](OC(C)=O)[C@@]2(C)[C@H]1C[C@@H](OC(C)=O)C1=C2CC[C@](C)(C=C)[C@@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O8/c1-9-25(5)12-10-18-22(23(25)35-17(4)30)19(33-15(2)28)14-20-26(6,24(31)32-8)13-11-21(27(18,20)7)34-16(3)29/h9,19-21,23H,1,10-14H2,2-8H3/t19-,20+,21+,23-,25+,26-,27-/m1/s1

> <INCHI_KEY>
HPLALXILNGTIHC-RRWJHGDBSA-N

> <FORMULA>
C27H38O8

> <MOLECULAR_WEIGHT>
490.593

> <EXACT_MASS>
490.256668184

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.291832775243485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,4S,4aS,7R,8S,9R,10aR)-4,8,9-tris(acetyloxy)-7-ethenyl-1,4a,7-trimethyl-1,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydrophenanthrene-1-carboxylate

> <JCHEM_LOGP>
2.9562713003333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.430388388300108

> <JCHEM_POLAR_SURFACE_AREA>
105.2

> <JCHEM_REFRACTIVITY>
126.68430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,4S,4aS,7R,8S,9R,10aR)-4,8,9-tris(acetyloxy)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2H-phenanthrene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      10.121   0.307   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.673  -0.220   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.673   1.760   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.494   3.437   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.804   4.771   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.804   2.104   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.184   4.771   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.414   6.105   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.874   6.105   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.184   7.438   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.874  -1.897   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.104  -3.231   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.874  -4.565   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.564  -3.231   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.510   3.643   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.742   2.920   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.689   4.459   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -2.102   2.197   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.156   0.658   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    9                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20                                                       
CONECT   20   19   21   30                                                  
CONECT   21   20    7   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   20   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₈O₈

Average Mass

490.5930 Da

Monoisotopic Mass

490.25667 Da

IUPAC Name

methyl (1R,4S,4aS,7R,8S,9R,10aR)-4,8,9-tris(acetyloxy)-7-ethenyl-1,4a,7-trimethyl-1,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydrophenanthrene-1-carboxylate

Traditional Name

methyl (1R,4S,4aS,7R,8S,9R,10aR)-4,8,9-tris(acetyloxy)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2H-phenanthrene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]1(C)CC[C@H](OC(C)=O)[C@@]2(C)[C@H]1C[C@@H](OC(C)=O)C1=C2CC[C@](C)(C=C)[C@@H]1OC(C)=O

InChI Identifier

InChI=1S/C27H38O8/c1-9-25(5)12-10-18-22(23(25)35-17(4)30)19(33-15(2)28)14-20-26(6,24(31)32-8)13-11-21(27(18,20)7)34-16(3)29/h9,19-21,23H,1,10-14H2,2-8H3/t19-,20+,21+,23-,25+,26-,27-/m1/s1

InChI Key

HPLALXILNGTIHC-RRWJHGDBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lycopus europaeus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 16-oxosteroids. These are steroid derivatives carrying a C=O group at the 16-position of the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

16-oxosteroids

Alternative Parents

Substituents

Pimarane diterpenoid
Diterpenoid
16-oxosteroid
Phenanthrene
Hydrophenanthrene
Tetracarboxylic acid or derivatives
Methyl ester
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.96	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	105.2 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.68 m³·mol⁻¹	ChemAxon
Polarizability	52.29 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7778843

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9496922

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,4s,4as,7r,8s,9r,10ar)-4,8,9-tris(acetyloxy)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate (NP0329896)

MOL for NP0329896 (methyl (1r,4s,4as,7r,8s,9r,10ar)-4,8,9-tris(acetyloxy)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)

3D MOL for NP0329896 (methyl (1r,4s,4as,7r,8s,9r,10ar)-4,8,9-tris(acetyloxy)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)

3D SDF for NP0329896 (methyl (1r,4s,4as,7r,8s,9r,10ar)-4,8,9-tris(acetyloxy)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)

3D-SDF for NP0329896 (methyl (1r,4s,4as,7r,8s,9r,10ar)-4,8,9-tris(acetyloxy)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)

PDB for NP0329896 (methyl (1r,4s,4as,7r,8s,9r,10ar)-4,8,9-tris(acetyloxy)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)

3D PDB for NP0329896 (methyl (1r,4s,4as,7r,8s,9r,10ar)-4,8,9-tris(acetyloxy)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)

SMILES for NP0329896 (methyl (1r,4s,4as,7r,8s,9r,10ar)-4,8,9-tris(acetyloxy)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)

INCHI for NP0329896 (methyl (1r,4s,4as,7r,8s,9r,10ar)-4,8,9-tris(acetyloxy)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)

Structure for NP0329896 (methyl (1r,4s,4as,7r,8s,9r,10ar)-4,8,9-tris(acetyloxy)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)

3D Structure for NP0329896 (methyl (1r,4s,4as,7r,8s,9r,10ar)-4,8,9-tris(acetyloxy)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)